59377-20-7Relevant academic research and scientific papers
Synthesis, analgesic and anti-inflammatory activity of 4-(2-phenoxyphenyl) semicarbazones
Rineh, Ardeshir,Mahmoodi, Nosratollah,Abdollahi, Mohammad,Foroumadi, Alireza,Sorkhi, Maedeh,Shafiee, Abbas
, p. 409 - 415 (2008/12/21)
A series of 4-(2-phenoxyphenyl)semicarbazones was synthesized and evaluated for their analgesic and anti-inflammatory activities. Several compounds (e.g. 10h, 10i, and 11i) were found to be more potent than the reference drug mefenamic acid in the formalin test. Based on the results of an anti-inflammatory study, 1-(1-(2,5-dimethoxyphenyl)ethylidene)-4-(2- phenoxyphenyl)semicarbazide 11i was the most active compound.
Selective muscarinic antagonists. II. Synthesis and antimuscarinic properties of biphenylylcarbamate derivatives
Naito, Ryo,Takeuchi, Makoto,Morihira, Koichiro,Hayakawa, Masahiko,Ikeda, Ken,Shibanuma, Tadao,Isomura, Yasuo
, p. 1286 - 1294 (2007/10/03)
A novel series of biphenylylcarbamate derivatives were synthesized and evaluated for binding to M1, M2 and M3 receptors and for antimuscarinic activities. Receptor binding assays indicated that biphenyl-2-ylcarbamate derivatives had high affinities for M1 and M3 receptors and good selectivities for M3 receptor over M2 receptor, indicating that the biphenyl-2-yl group is a novel hydrophobic replacement for the benzhydryl group in the muscarinic antagonist field. In this series, quinuclidin-4-yl biphenyl-2-ylcarbamate monohydrochloride (81, YM-46303) exhibited the highest affinities for M1 and M3 receptors, and selectivity for M3 over M2 receptor. Compared to oxybutynin, YM-46303 showed approximately ten times higher inhibitory activity on bladder pressure in reflexly-evoked rhythmic contraction, and about 5-fold greater selectivity for urinary bladder contraction against salivary secretion in rats. Moreover, selective antagonistic activity was also observed in vitro. Further evaluation of antimuscarinic effects on bradycardia and pressor in pithed rats, and on tremor in mice, showed that YM-46303 can be useful for the treatment of urinary urge incontinence as a bladder-selective M3 antagonist with potent activities and fewer side effects.
Peroxydicarbonate-mediated oxidation of N-(ortho-aryloxyphenyl) and N-(ortho-arylaminophenyl)aldimines
Leardini, Rino,McNab, Hamish,Nanni, Daniele
, p. 12143 - 12158 (2007/10/02)
Imidoyl radicals 5, obtained from imines 1 by hydrogen abstraction with di-iso-propyl peroxydicarbonate (DPDC), give dibenzoxazepines through 7-membered ring closure. A competitive 6-membered cyclisation leads to intermediate spirocyclohexadienyl radicals that rearrange to aryloxy radicals; this process entails a novel 1,5-aryl radical translocation from an oxygen to a carbon atom and leads to benzophenones, benzoxazoles, and biphenyls. The possibility that the oxazepines arise from rearrangement of the 6-membered-ring-closure intermediates is discussed. With imine 1e, the formation of 5e occurs to a minor extent owing to a side-reaction of the iso-propoxycarbonyloxy radicals, which give rise to an intermolecular aromatic ipso-substitution on the benzenic ring linked to the two oxygen atoms. The 1,5-aryl migration can also be observed with imidoyl radicals generated by radical addition to 2-phenoxyisocyanobenzene. In contrast, the reactions of imines 2 with DPDC do not afford imidoyl radicals, as abstraction of the iminic hydrogen is slower than oxidation of the methyl group: this process entails the formation of carbamoyl radicals, which cyclise onto the carbonitrogen double bond, furnishing quinoxalinone derivatives, or loose carbon monoxide to yield benzimidazoles through ring closure of aminyl radicals. A novel cyclisation of a nitrogen-centred radical onto a formamido group could account for the formation of a benzimidazolinone derivative.
5-Hydroxytryptamine (5-HT3) Receptor Antagonists. 3. Ortho-Substituted Phenylureas
Bermudez, Jose,Dabbs, Steven,King, Frank D.
, p. 1932 - 1935 (2007/10/02)
A novel series of potent 5-HT3 receptor antagonists, ortho-substituted phenylureas 6a-z, is described in which the 5-membered ring of the previously reported indazoles and indolines has been replaced by an intramolecular hydrogen bond.High potency was found both for carbamate 6a and urea 6b.Granatane 6c was less potent than the equivalent tropane.Phenylurea 11c lacking the ortho substituent was inactive.Whereas further substitution could not be tolerated in the aromatic ring, activity was retained with a range of O-alkyl groups, compounds 6k-t.In addition, good activity was found for ortho ester 6u and sulfonamide 6x.The ortho-substituted phenylureas can therefore be regarded as bioisosteres of the 6,5-heterocycles indole, indazole, and indoline.
